Phenylacetyl chloride → Geranyl phenylacetate

HRID 266667

Reaktionsgleichung

Reaktionsgleichung von HRID 266667
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].[OH:12][CH2:13]/[CH:14]=[C:15](/[CH3:22])\[CH2:16][CH2:17][CH:18]=[C:19](C)C.C(N(CC)CC)C.C1(CC(Cl)=O)C=CC=CC=1>ClCCl>[C:15]1([CH2:14][C:13]([O:11][CH2:10]/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])\[CH3:8])=[O:12])[CH:16]=[CH:17][CH:18]=[CH:19][CH:22]=1

Komponenten

6

Edukt 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 637566GeraniolHCID 643820Nerol

Produkt 1

HCID 5366044Geranyl phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of geraniol and nerol (approximately 70:30 by weight) in the amount of 51.02 g (0.324 mol) and triethylamine in the amount of 33.13 g (0.324 mol) are combined with 275 mL of dichloromethane. The reaction mixture is treated with a solution of phenylacetyl chloride in the amount 51.14 g (0.324 mol) dissolved in 100 ml of dichloromethane over 1 h. After heating to reflux for 1 h, the product mixture is cooled to room temperature, washed with 100 mL of brine twice, 100 mL of saturated NaHCO3 solution twice, 100 mL of water, and dried over MgSO4. The filtrate is concentrated by rotary evaporation followed by Kugelrohr distallation. Purification of the product by column chromatography provides a colorless oil. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13C and 1H NMR.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureto reflux for 1 h
  3. washwashed with 100 mL of brine twice
  4. dry with material100 mL of saturated NaHCO3 solution twice, 100 mL of water, and dried over MgSO4
  5. concentrationThe filtrate is concentrated by rotary evaporation
  6. customPurification of the product by column chromatography
  7. customprovides a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-eb3c45aaed5a4d5baa00536823867005
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652205

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